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The engagement in litigation is synonymous with risk and the inherent probability that the case brought forth against the defendant may fail. The burden of costs imposed on a party who has unreasonably rejected an otherwise reasonable offer of compromise has been a long established rule of judicial engagement. The increasing cost of litigation coupled with the sheer number of claims that are presented to the Courts each year compels the need for adverse sanctions to be enforced against those who do not attempt to reasonably settle a dispute prior to trial. It has been argued that the settlement of such disputes can often lead parties to a cynical view of the judicial system and the inherent belief that justice was not adequately achieved. Such contentions are principally unfounded given that all settlements are at the free will of each litigant and are decided with the guidance of their legal counsel in respect to an assessment of costs if the matters were to proceed to trial. The importance of a pragmatic costs judgment, in addition to a realistic assessment of the strength of each party’s arguments, forms the critical determination of whether an offer of compromise is accepted or rejected. The reliance on legal practitioners in this regard is paramount in balancing the outcome the litigant desires against the probability of success or failure in the trial itself.